Windsor County Vacation Packages
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Your Windsor County Vacation
With a Windsor County vacation package, you can forget about planning hassles and instead focus on experiencing everything this exciting destination has on offer. Begin your trip to Windsor County with some time exploring Ludlow visiting popular sights like Weston Playhouse and Lake Rescue. Norwich is another top city that lures crowds from near and far. Quechee Gorge Bridge and Quechee Gorge Village are two of the leading places to see in this destination. From the instant you book your Windsor County vacation to the second you come back home, Expedia will take care of you each step of the way.
Top vacation destinations in Windsor County
Ludlow
Woodstock
White River Junction
Cavendish
Windsor
Top Windsor County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Lake Bomoseen Lodge
CA $1,116
per person
Nov 30 - Dec 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Rutland (RUT)
9.4/10 Exceptional! (999 reviews)
We had a great stay here! This was a long weekend girls' trip. There was easy access to the lake, a clean property, and really good food on-site at the restaurant with live music. The sweet potato hummus is a must-try! The pool was refreshing with plenty of activities to choose from: cornhole, volleyball, and pickleball. There's a little ice cream shop open in the afternoon. You can take a ride on the catamaran or the tiki boat for a small fee. Our stay was reasonably priced. The staff was friendly. Just an easy, no-nonsense, enjoyable getaway. We loved it and are thinking about making this a yearly girls' trip! Thank you so much for a great stay!
Reviewed on Sep 17, 2026
The Landgrove
CA $1,297
per person
Nov 6 - Nov 11
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
8.6/10 Excellent! (7 reviews)
We arrived late, there was someone there to greet us. I had left a personal item, they were kind enough to call and mail it to us.
Reviewed on Oct 3, 2026
The Mountain Top Inn & Resort
CA $1,482
per person
Nov 30 - Dec 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Rutland (RUT)
9/10 Wonderful! (124 reviews)
Oh wow!! I would stay here again tomorrow! Beautiful property, restaurant has amazing food and convenient location. We stayed in the Long View Barn, the 60 mile view was even more spectacular than we imagined!
Reviewed on Oct 1, 2026
Bentley House Bed and Breakfast
CA $1,223
per person
Nov 6 - Nov 11
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
10/10 Exceptional! (27 reviews)
We enjoyed our stay in this cozy B&B the owner are accommodating and the place is clean. Breakfast is delicious!!!
Reviewed on Oct 3, 2026
Windsor County Hotel Deals
Align Inn Vermont
5817 Woodstock Rd Quechee VT
CA $314
CA $346 total
Oct 19 - Oct 20
includes taxes & fees
9.4/10 Exceptional! (1,370 reviews)
"Not bad, but staff just do not see you."
Reviewed on Oct 4, 2026
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
CA $626
CA $751 total
Nov 2 - Nov 3
includes taxes & fees
9.4/10 Exceptional! (612 reviews)
"Dinner at their restaurant was very good- the best fish(halibut) I’ve ever had. The rooms are small but very clean and decorated with thought. The continental breakfast was also very good. The staff was helpful and friendly. We enjoyed our stay very much."
Reviewed on Oct 3, 2026
Jackson Gore Village, A Vail Resorts Property
111 Jackson Gore Road Ludlow VT
Fully refundableReserve now, pay when you stay
CA $257
CA $312 total
Oct 26 - Oct 27
includes taxes & fees
8.6/10 Excellent! (910 reviews)
"The room was clean and the front desk staff were very neat and pleasant, but the bathroom water pressure was way too weak. There was also no vending machine, so there was nowhere to get water—it felt like you'd need to bring all your own food and drinks if you stay there. Overall, it was quiet and ..."
Reviewed on Oct 2, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
How much does a Windsor County vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Windsor County from just CA $1,116. And the more you bundle, the more cash you save. The vacation of your dreams has never been more affordable.
How do I get a cheap travel package to Windsor County?
You'll save a ton of money if you bundle your hotels, car rentals and flights into a Windsor County travel package. Sometimes cheap packages mean fewer choices. But not with Expedia. We offer over 550 airlines and 1,000,000 hotels all over the world, which means you'll always have plenty of variety to choose from. Want to save even more? Add some exciting activities to your package deal to unlock even more bargains! After all, travel is about more than simply getting to your destination.
Where should I stay in Windsor County?
Okemo Mountain Resort is one of the key things that lures people to Windsor County, so it makes perfect sense that many decide to book their hotel in Ludlow.
What are the top hotels in Windsor County?
When it comes to hotels in Ludlow, Super 8 by Wyndham White River Junction and Holiday Inn Express Hotel & Suites White River Junction, an IHG Hotel are two terrific options. If you're spending time in Plymouth, Hotel Coolidge and White River Inn and Suites will make you feel right at home.
How far in advance should I book my Windsor County vacation?
It depends on the airline, but you can usually browse through international fares on Expedia up to a year in advance. While it's advisable to book ahead of time, lucky customers will sometimes find a cheaper flight only weeks before their intended journey.
What does an Expedia Windsor County travel package include?
It comes down to what you're looking for. If you're traveling by yourself, you might decide to bundle hotels and flights. Bringing the entire family to Windsor County? A travel package that includes hotels, rental cars and flights might suit you better. Expedia gives you the freedom and flexibility to tailor your travel package.
What should I know before booking a Windsor County travel package?
You'll save big with an Expedia travel package. Combine your flights, rental cars and hotels and be rewarded with great discounts. Hotels aren't your only choice, however. Book with us and take your pick of beachside condos, chalets in the middle of mountains and even glamping tents!
Can I choose my airline with a Windsor County Expedia vacation package?
Most definitely. Expedia has more than 550 partner airlines to select from across the world. With so many choices, finding the ideal carrier to fly you to Windsor County will be a snap.
If I'm not able to travel, can I cancel my Windsor County vacation package?
We get it — unexpected stuff happens. If you've locked in a Windsor County vacation package and need to amend or cancel it, we can help. It's always worth browsing our Customer Service Portal first for information. But generally, if you've booked your package within 24 hours, you may be able to amend or cancel your itinerary free of charge. If it's been more than 24 hours, your hotel, airline or car rental company may impose a charge.
Stay near popular Windsor County attractions
Okemo Mountain Resort
9.2/10 (510 reviews)
Hit the slopes in Ludlow with a visit to Okemo Mountain Resort. Discover the mountain views in this romantic area.
Photo by Mike Gauthier
Quechee Gorge Bridge
9.2/10 (580 reviews)
Quechee Gorge Bridge is just one of the places to see in White River Junction, so why not enjoy the other things to explore during your travels? Wander the riverfront in this quaint area.
Photo by George Sykes
King Arthur Baking Company
9.4/10 (178 reviews)
You can enjoy retail therapy at King Arthur Baking Company during your stay in Norwich. While you're in the area, stroll along the riverfront.
Photo by Ed Gaffny
Quechee Gorge Village
9.0/10 (288 reviews)
You can enjoy retail therapy at Quechee Gorge Village during your trip to Quechee. Amble around the area's riverfront or seek out the ski slopes.
Photo by William E Berry Jr.
Mount Ascutney
8.8/10 (27 reviews)
Commune with nature and explore the great outdoors at Mount Ascutney during your travels in Brownsville. You can seek out the ski slopes while in the area.
Billings Farm and Museum
9.2/10 (84 reviews)
You can study the exhibits at Billings Farm and Museum, a museum with a storied past, during your trip to Woodstock. Wander the riverfront in this quaint area.
Simon Pearce Mill
9.0/10 (80 reviews)
Learn about the local history of Quechee when you spend time at Simon Pearce Mill. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
